| Width | 225px |
|---|---|
| Routes of administration | Oral[1] |
| Class | Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
| Atc prefix | None |
| Duration of action | ~8 hours[1] |
| Cas number | 69294-23-1 |
| Pubchem | 12140147 |
| Chemspiderid | 23256805 |
| Chembl | 365711 |
| Synonyms | 4C-DOB; DOB-B; 4-Bromo-2,5-dimethoxy-α-ethylphenethylamine |
| Iupac name | 1-(4-bromo-2,5-dimethoxyphenyl)butan-2-amine |
| C | 12 |
| H | 18 |
| Br | 1 |
| N | 1 |
| O | 2 |
| Smiles | CCC(CC1=CC(=C(C=C1OC)Br)OC)N |
| Stdinchi | 1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3 |
| Stdinchikey | QQPRORAZQWLMTQ-UHFFFAOYSA-N |
| Melting point | 204 |
| Melting high | 206 |
4C-B, also known as 4C-DOB or DOB-B, as well as 4-bromo-2,5-dimethoxy-α-ethylphenethylamine, is a lesser-known psychedelic drug of the phenethylamine, phenylisobutylamine, and 4C families related to 2C-B (the 2C analogue) and DOB (the DOx analogue).[2]
It is briefly mentioned in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known And Loved), but was never tested by Shulgin.[3] Subsequently, the drug was tested by Daniel Trachsel and colleagues, and was found to be active in a dose range of 50 to 80 mg orally with a duration of around 8 hours.[1] It produced pronounced psychedelic effects, though with generally milder effects than 2C-B or DOB.[1]
The drug is a reasonably potent serotonin 5-HT2A receptor partial agonist with a Ki of 7.6 nM, but has relatively low efficacy (15% relative to 5-HT).[4]
4C-B is a controlled substance in Canada under phenethylamine blanket-ban language,[5] but is not explicitly controlled in the United States.[6]
See also
References
- ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4.
Das α-Ethylhomologon von 2C-B (6) trägt den Namen (303; auch 4C-B) und wurde von Rausch eingehender untersucht [140, 145]. Es vermochte eine ausgeprägte psychedelische Wirkung mit Bewusstseinsvertiefung, Euphorie und Sensationen besonders im Bereich des Tastsinns hervorzurufen (50—80mg, rund acht Stunden Wirkdauer). Visuelle Pseudohalluzinationen traten kaum auf. Das Iodoanalogon DOI-B (304) wurde nur bis zu einer Dosierung von 4mg geprüft und zeigte dabei keinerlei Wirkungen [8].
- ^ Standridge RT, Howell HG, Tilson HA, Chamberlain JH, Holava HM, Gylys JA, Partyka RA, Shulgin AT (February 1980). "Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes". Journal of Medicinal Chemistry. 23 (2): 154–62. doi:10.1021/jm00176a010. PMID 7359529
- ^
- ^ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–41. doi:10.1021/jm040082s. PMID 15537358
- ^ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
- ^ "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)", United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026